Potassium Carbonate → 4-Bromo-2-tert-butyl-difluoromethoxy-benzene

HRID 2390790Notes

Reaction equation

HRID 2390790 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:20]([F:27])([F:26])C(OCC)=O>CN(C=O)C.CCOC(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:20]([F:27])[F:26])=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 67843Acetic acid, 2-chloro-2,2-difluoro-, ethyl esterHCID 970684-Bromo-2-tert-butylphenol

Product 1

HCID 672864304-Bromo-2-tert-butyl-difluoromethoxy-benzeneYield 33.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

step 1—To a mixture of 4-bromo-2-tert-butyl-phenol (640 mg, 2.795 mmol) and potassium carbonate (1.20 g, 8.682 mmol) in DMF (8 mL) was added ethyl chlorodifluoroacetate (1.1 mL, 8.687 mmol). The reaction was heated to 80° C. overnight then cooled to RT, and diluted with EtOAc and water. The organic layer was washed with water, with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 column eluting with hexane to afford 259 mg (33%) of 4-bromo-2-tert-butyl-difluoromethoxy-benzene (20) as a colorless oil.

Workup

  1. temperaturethen cooled to RT
  2. washThe organic layer was washed with water, with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by SiO2 column
  7. washeluting with hexane

Sources & evidence

ORD record
ord-ffe164955dc345f2b337eead1082d239
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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